The conversion of mixed N,O-diacylated 2-aminophenols to 2-substituted benzoxazoles

Authors
DeLuca, MR Taraporewala, IB Kerwin, SM
Citation
Mr. Deluca et al., The conversion of mixed N,O-diacylated 2-aminophenols to 2-substituted benzoxazoles, HETEROCYCLE, 51(5), 1999, pp. 979-982
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
51
Issue
5
Year of publication
1999
Pages
979 - 982
Database
ISI
SICI code
0385-5414(19990501)51:5<979:TCOMN2>2.0.ZU;2-E
Abstract
When N,O-diacylated 2-aminophenols that have different acyl substituents on nitrogen and oxygen are treated with p-toluenesulfonic acid in refluxing x ylenes, mixtures of benzoxazoles are produced. The major product is the ben zoxazole in which the substituent at the 2-position is derived from the acy l group on nitrogen. This product may arise from an unusual case of acid-me diated neighboring amido-group assisted hydrolysis.